A Tribe Called Quest: The Low End Theory

Q-Tip begins Tribe’s second and jazziest album by relaying that conversation with his father, and for the ensuing 45 minutes, he, Phife Dawg, and Ali Shaheed Muhammad strengthen the two genres’ connection. There are acoustic bass-driven grooves, multiple shout-outs to jazz and its pioneers, and even a guest appearance by Ron Carter, a legendary double bassist who played with everyone from Miles Davis to Gil Scott-Heron. Predecessor People’s Instinctive Travels and the Paths of Rhythm may have had the hits (“Bonita Applebum” and “Can I Kick It?”), and follow-up Midnight Marauders may be the group’s most well-rounded album, but neither is as influential to the jazz rap genre as Low End Theory.

Us3: Hand on the Torch

Tribe may have mimicked Blue Note’s iconic aesthetic for their “Jazz (We’ve Got)” single artwork, but U.K.-group Us3 one-upped them by becoming the first hip-hop act to sign with the label. Their 1993 debut fused live instrumentation with samples culled exclusively from the Blue Note archive, most notably on aptly named hit single “Cantaloop (Flip Fantasia),” which flipped Herbie Hancock’s “Cantaloupe Island.” As a result, Hand on the Torch’s arrangements jump off the page more than any previous jazz rap album. The rapping isn’t always up to par with Us3’s contemporaries, but the album’s flow and inclusion of a wide variety of jazz styles makes it a must-hear. Original print isn't hard to come by, but Blue Note also just reissued a deluxe edition last year.

The Pharcyde: Bizarre Ride II The Pharcyde

One of the first West Coast acts to emerge with a jazzy sound, the Pharcyde, were a refreshingly light-hearted counterpoint to South Central L.A.’s many gangster rappers in the early ’90s. The group’s four MCs linked up with Spanish-born producer and piano prodigy J-Swift for their landmark 1993 debut, which is undoubtedly the most fun album on this list. Bizarre Ride II is the sound of old friends shooting the shit and shit-talking, complete with cypher-style lyrical workouts and “Ya Mama” jokes, all of which is filtered through an immediately perceptible haze of pot smoke and stale beer. Warm samples of Weather Report, Herbie Mann, John Coltrane, and other jazz greats contribute as much to this freewheeling atmosphere as the schoolyard lyrics do, making for a seemingly bottomless supply of good vibes.

Souls of Mischief: 93 ‘til Infinity

Another key alt-rap fixture in mid-’90s California was the Bay Area’s Hieroglyphics collective, the high-water mark of which is Souls of Mischief’s 1993 debut. You probably know the breezy, vibraphone-driven title track built atop a Billy Cobham sample, but that’s only the tip of the iceberg. From the opening track, “Let ’Em Know,” Souls set out to liven up the blueprint created by Tribe on Low End Theory, adding live acoustic bass and even some horns to a handful of tracks, and handing off sample-heavy production duties to Hiero mainstays like Del The Funky Homosapien and Domino. They expand on the chummy atmosphere Pharcyde created on Bizarre Ride II with songs centered around boasts of sexual and lyrical prowess, but also provide a heavy dose of East Coast-style realism on murder tale “Anything Can Happen” and education critique “Tell Me Who Profits.” 93 ‘til Infinity’s sound falls in the center of a Venn diagram of Native Tongues, Pete Rock style boom-bap, and West Coast backpack rap and thus all of those scenes’ jazz reverence is ingrained in its DNA.

Jeru The Damaja: The Sun Rises in the East

DJ Premier might have more of a claim than anyone else to the title of godfather of jazz rap, as his work on Gang Starr’s 1989 debut, No More Mr. Nice Guy, set off the early ’90s seismic shift from classic soul and funk samples to jazzier, more obscure territory. For my money though, his most delectable jazz flips came five years later, on Jeru The Damaja’s 1994 debut album. Jeru had been knocking around Brooklyn rap for a few years, guesting on Gang Starr’s 1992 album Daily Operation and dropping a few singles with Preemo before they decided to link up for a full album. As an MC, the in-your-face Jeru couldn’t have been more different than suave, laid-back Guru, and Premier catered to this by swapping out his usual smooth grooves for freer, more avant-garde jazz textures. Listen to the off-key piano stabs on “D Original,” Roy Ayers’ trippy vibraphone on “Mental Stamina,” or Shelly Manne’s oddball drum experiments on “Come Clean” — to this day, it’s some of the most ambitious jazz sampling in hip-hop.

Digable Planets: Blowout Comb

Digable Planets are best-known for one of the most popular jazz rap singles of all-time, 1992’s “Rebirth of Slick (Cool Like Dat),” but their crowning achievement is a deeper, much weirder exploration of jazz. The group’s second and final album is a full band workout with songs that regularly extend past the five-minute mark, eschew standard structure, bury vocals in the mix, and meditate upon Afrocentrism and urban culture. Blowout Comb is a dark and intoxicating epic, the furthest thing from Tribe’s easily-digestible jazz postcards. It acts as an anthropological survey of Brooklyn’s vibrant thinking man’s rap scene of the mid-’90s, with both Guru and Jeru The Damaja showing up for guest verses, and songs that touch on neighborhood barbershops, graffiti culture and NYC’s five boroughs. The group only recently reunited for a string of concerts, but in their absence, founding member Ishmael Butler has taken Blowout Comb’s approach to even spacier realms with his Shabazz Palaces project.

The Roots: Do You Want More?!!!??!

The Roots’ 1995 sophomore album is rarely cited as their best (that honor is usually reserved for the 1999 opus Things Fall Apart), but it is their most devoted to jazz. You can tell from Questlove’s herky-jerky rhythms and Scott Storch’s subtle keyboard flourishes that the group had been studying the moves of their jazz rap contemporaries, but as a well-oiled full band, they were able to bring the music back closer to its roots (no pun intended). Do You Want More?!!??! is the only album on this list with live scatting, a cappella harmonies, and drum solos, and it’s also the only jazz album I know that features beatboxing. You won’t find another group that straddles the line between rap and jazz as effortlessly as The Roots.

Guru: Jazzmatazz Volume 1

Guru was just as devoted as DJ Premier to making jazz an integral part of Gang Starr’s sound, but his main side project delved even further into the genre than any of Premo’s later work. He described the first of his four Jazzmatazz albums as “an experimental fusion of hip-hop and live jazz,” and it was certainly ambitious enough to live up to the title. Jazz greats such as Donald Byrd, Roy Ayers, Branford Marsalis, and Lonnie Liston Smith conduct melodic workouts over classic hip-hop drum breaks, and Guru intersperses his rapping with guest singers and extended instrumental passages, making for a much more even 50/50 split of the genres than any Gang Starr album aspired to be. Hopefully you were lucky enough to score a copy of Vinyl Me, Please’s limited edition reissue, but if not, you can still scoop Virgin Records’ 2016 reissue.

Madlib: Shades of Blue

Although it only features rapping on one song, Shades of Blue is a cornerstone of jazz rap for two reasons. For one, Madlib is one of the most inventive samplers of all-time, and secondly, Blue Note turned him loose on their archives for this album, with a resulting total of over 20 samples from their ’60s and ’70s catalog. Punctuated by snippets of interviews from documentary Blue Note: A Story of Modern Jazz, the resulting album plays like an inventive, interactive crash course in the label’s varied sounds, with Madlib as the hip professor. The Beat Konducta was already well-versed in flipping “old jazz standards,” as MF Doom would later say on Madvillainy, by the time of Shades of Blue’s 2003 release, so getting recognized for that by the venerable label was quite the honor. He’s gone on to create a full band jazz side project, Yesterday’s New Quintet, and conduct similar album-length experiments with dub, African music, Brazilian music, Bollywood soundtracks and even Nas and JAY-Z’s catalogs.

Kendrick Lamar: To Pimp a Butterfly

Released a good 20 years after jazz rap’s heyday, and twelve after the second-newest album on this list, To Pimp a Butterfly as much marks a culmination of the genre as it heralds a new era. He recruited a murderer’s row of musicians who were raised on both genres — bass virtuoso Thundercat, multi-instrumentalist Terrace Martin, pianist Robert Glasper, saxophonist Kamasi Washington and producer Flying Lotus — so the resulting album doesn’t feel as much like a marriage between hip-hop and jazz as it does a child of the two genres copulating with more modern strains of astral funk and trap music. These are people who grew up idolizing Q-Tip and Miles Davis with equal reverence, and it shows. Jazz rap is the lowest common denominator of all parties involved in this album, and along with it they each bring their own expertise, such as FlyLo’s Brainfeeder electronica or Martin’s G-funk masterclasses.

In its wake, To Pimp a Butterfly has sown the seeds for a modern-day jazz rap renaissance, with a whole new wave of artists picking up the genre’s building blocks and playing with them in ways never imagined in the ’90s. Chance The Rapper and The Social Experiment have added technicolor flair and gospel into the mix, Anderson .Paak smooths out jazz’s jagged edges into California cool, Mick Jenkins loosens up his wide-eyed street sermons, BADBADNOTGOOD shift from Waka Flocka Flame covers into structurally thrilling compositions, and Kamasi Washington’s massive The Epic stands as one of the 21st Century’s greatest achievements in jazz. Jazz rap looks a whole lot different these days, but it’s finally equaling the popularity of its ’90s peak.

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